Utilizing a condensation reaction between amine I and methyl propiolate to obtain pyridone III followed by reaction with potassium t-butoxide and oxygen in dimethyl sulfoxide, a convenient synthesis of 6-hydroxy-5,8-dioxocarbostyril (V) was achieved. Conversion of 8-hydroxycarbostyril via dinitro (XII) and diamino (XIIIa) intermediates provided the isomeric 7-hydroxy-5,8-dioxocarbostyril (XV). The structures assigned to hydroxyquinones V and XV received support from mass spectral and proton magnetic resonance studies.
ASJC Scopus subject areas
- Organic Chemistry